Facile and stereoselective synthesis of N-substituted benzotriazole with Baylis-Hillman adducts

Chinese Chemical Letters

Volumn 17, Issue 7, 2006, Pages 877-879

  Li, Jian ^a   Liu, Yun Kui ^c   Zhang, Yong Min ^b,d  

^a SHANGHAI UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^d SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Baylis Hillman adduct; Benzotriazole; N substituted

Indexed keywords

EID: 33748276443     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. (a) A. R. Katritzky, X. Lan, J. Z. Yang, et al., Chem. Rev., 1998, 98, 409.
2. (b) A. R. Katritzky, K. Manju, S. K. Singh, et al., Tetrahedron, 2005, 61, 2555.
3. (c) A. R. Katritzky, K. Suzuki, Z. Wang, Synlett, 2005, 1656.
4. (d) A. R. Katritzky, X. Lan, Chem. Soc. Rev., 1994, 23, 363.
5. nd ed., Pergamon Oxford, 2002.
6. (a) G. R. Martinez, K. A. M. Walker, D. R. Hirschfeld, et al., J. Med. Chem., 1992, 35, 620.
7. (b) M. C. Venuti, R. A. Stephenson, R. Alvarez, et al., J. Med. Chem., 1988, 31, 2136.
8. (c) Y. S. Lo, J. C. Nolan, T. H. Maren, et al., J. Med. Chem., 1992, 55, 4790.
9. For reviews, see: (a) E. Ciganek, Org. Reactions, 1997, 51, 201.
10. (b) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron, 1996, 52, 8001.
11. (c) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev., 2003, 103, 811.
12. For examples: (a) C. W. Cho, M. J. Krische, Angew. Chem., Int. Ed., 2004, 43, 6689.
13. (b) G. W. Kabalka, B. Venkataiah, G. Dong, J. Org. Chem., 2004, 69, 5807.
14. (c) G. W. Kabalka, B. Venkataiah, G. Dong, Tetrahedron Lett., 2003, 44, 4673.
15. (d) Y. M. Chung, J. H. Gong, T. H. Kim, J. N. Kim, Tetrahedron Lett., 2001, 42, 9023.
16. (e) M. Shi, J. K. Jiang, Y. S. Feng, Org. Lett., 2000, 2, 2397.
17. (a) J. Li, W. X. Qian, Y. M. Zhang, Tetrahedron, 2004, 60, 5793.
18. (b) J. Li, H. Xu, Y. M. Zhang, Tetrahedron Lett., 2005, 46, 1931.
19. (c) J. Li, X. X. Wang, Y. M. Zhang, Synlett, 2005, 1039.
20. 1H NMR appears obviously downfield to the aromatic ring proton in terms of the E-isomer, while that corresponding olefinic proton of Z-isomer often mixed with aromatic ring proton or appeared upfield.
21. All Baylis-Hillman adducts are prepared from aromatic aldehydes and methyl acrylate according to literature: H. M. R. Hoffman, J. Rabe, Angew. Chem., Int. Ed., 1983, 22, 795.
22. +, 25), 220 (94), 129 (100), 115 (61), 77 (59).